Diazomethane → HCID 86733078, compound

HRID 1730960Notes

Reaction equation

HRID 1730960 reaction equation
[N+:1](=[CH2:3])=[N-:2].N(CNC(N)=O)=O.[O:11]([C:18]1[CH:19]=[C:20]([C:24]([CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:25][N:26]=1)[C:21](Cl)=[O:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCOCC>[O:11]([C:18]1[CH:19]=[C:20]([C:21](=[O:22])[CH:3]=[N+:1]=[N-:2])[C:24]([CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:25][N:26]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 9550DiazomethaneHCID 104823Urea, (nitrosomethyl)-HCID 53724591HCID 53724591, compound

Product 1

HCID 86733078HCID 86733078, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To an ethereal solution of diazomethane prepared from nitrosomethylurea (2.0 g) and ether (25 ml), a solution of the said 2-phenoxy-5-ethoxycarbonylethylisonicotinoyl chloride (1.05 g) in anhydrous ether (10 ml) is added dropwise at 0° to 3° C, and the resultant mixture is stirred at 10° to 15° C for 1 hour. The reaction mixture is evaporated under reduced pressure to remove the ether. The residue is chromatographed on a column of neutral alumina/50 % benzene-n-hexane, whereby 2-phenoxy-4-diazoacetyl-5-ethoxycarbonylethylpyridine (830 mg) is obtained. This substance is recrystallized from ether/n-hexane to give crystals melting at 77° to 79° C (decomp.). IR (CCl4): 2120, 1745 cm-1.

Workup

  1. customThe reaction mixture is evaporated under reduced pressure
  2. customto remove the ether
  3. customThe residue is chromatographed on a column of neutral alumina/50 % benzene-n-hexane

Sources & evidence

ORD record
ord-52716fd7cffe4c7d843b26f0673fd6d5
Source dataset
uspto-grants-1976_11
Patent number
US03994908

Reaction notes

Loading…